1-(4,6-dimethoxy-3-methyl-1H-indol-2-yl)-2-(pyrrolidin-1-yl)ethane-1,2-dione | 180859-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(4,6-dimethoxy-3-methyl-1H-indol-2-yl)-2-(pyrrolidin-1-yl)ethane-1,2-dione
• 英文别名: 1-(4,6-dimethoxy-3-methyl-1H-indol-2-yl)-2-pyrrolidin-1-ylethane-1,2-dione
• CAS: 180859-49-8
• 化学式: C₁₇H₂₀N₂O₄
• 分子量: 316.357
• InChiKey: FVDFPNVKKOUPSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4,6-dimethoxy-3-methyl-1H-indol-2-yl)-2-(pyrrolidin-1-yl)ethane-1,2-dione 生成 2-(4,6-Dimethoxy-3-methyl-1H-indol-2-yl)-2-hydroxy-1-pyrrolidin-1-yl-ethanone
  参考文献：
  名称：

  Formation of C-Amido-calix[3]indoles from 2′- and 7′-Indolylglyoxylamides

  摘要：

  A range of 2'- and 7'-indolylglyoxylic amides 1 and 2, derived from 3-(4'-chlorophenyl)-4,6-dimethoxyindole, have been reduced to the corresponding alcohols 3 and 4 respectively. On treatment with acid, these alcohols underwent trimerisation to give the calix[3]indoles 8. The major conformer was generally the flattened partial cone, but in certain cases the cone conformers could be detected and even isolated. The related 2'-indolylglyoxylic amides 13, derived from 4,6-dimethoxy-3-methylindole, were also converted into calix[3]indoles 15. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00774-2
• 作为产物：
  描述：

  乙基二甲氧基喹啉羟酸酯 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.5h， 生成 1-(4,6-dimethoxy-3-methyl-1H-indol-2-yl)-2-(pyrrolidin-1-yl)ethane-1,2-dione
  参考文献：
  名称：

  一些4,6-二甲氧基吲哚与草酰氯的反应

  摘要：

  使3-（4'-氯苯基）-4,6-二甲氧基吲哚1与草酰氯反应，以不同比例根据溶剂和反应温度得到相应的2-和7-乙二酰氯衍生物。乙醛酰氯2和3分别转化为相关的乙醛酸，也分别转化为各种乙醛酸酯和酰胺4和5。

  DOI：

  10.1016/0040-4020(96)00441-3

文献信息

• Synthesis and biological activity of novel mono-indole and mono-benzofuran inhibitors of bacterial transcription initiation complex formation
  作者：Marcin Mielczarek、Ruth V. Thomas、Cong Ma、Hakan Kandemir、Xiao Yang、Mohan Bhadbhade、David StC. Black、Renate Griffith、Peter J. Lewis、Naresh Kumar

  DOI：10.1016/j.bmc.2015.02.037

  日期：2015.4

  Our ongoing research focused on targeting transcription initiation in bacteria has resulted in synthesis of several classes of mono-indole and mono-benzofuran inhibitors that targeted the essential protein-protein interaction between RNA polymerase core and sigma(70)/sigma(A) factors in bacteria. In this study, the reaction of indole-2-, indole-3-, indole-7- and benzofuran-2-glyoxyloyl chlorides with amines and hydrazines afforded a variety of glyoxyloylamides and glyoxyloylhydrazides. Similarly, condensation of 2- and 7-trichloroacetylindoles with amines and hydrazines delivered amides and hydrazides. The novel molecules were found to inhibit the RNA polymerase-sigma(70)/sigma(A) interaction as measured by ELISA, and also inhibited the growth of both Gram-positive and Gram-negative bacteria in culture. Structure-activity relationship (SAR) studies of the mono-indole and mono-benzofuran inhibitors suggested that the hydrophilic-hydrophobic balance is an important determinant of biological activity. (C) 2015 Elsevier Ltd. All rights reserved.
• Reaction of some 4,6-dimethoxyindoles with oxalyl chloride
  作者：David StC. Black、Naresh Kumar、Darryl B. McConnell

  DOI：10.1016/0040-4020(96)00441-3

  日期：1996.6

  3-(4′-Chlorophenyl)-4,6-dimethoxyindole 1 undergoes reaction with oxalyl chloride to give the corresponding 2-and 7-glyoxyloyl chloride derivatives in differing proportions depending on the solvent and reaction temperature. The glyoxyloyl chlorides 2 and 3 were converted into the related glyoxylic acids, and also a wide range of glyoxylic esters and amides 4 and 5 respectively.

  使3-（4'-氯苯基）-4,6-二甲氧基吲哚1与草酰氯反应，以不同比例根据溶剂和反应温度得到相应的2-和7-乙二酰氯衍生物。乙醛酰氯2和3分别转化为相关的乙醛酸，也分别转化为各种乙醛酸酯和酰胺4和5。
• Formation of C-Amido-calix[3]indoles from 2′- and 7′-Indolylglyoxylamides
  作者：David StC Black、Naresh Kumar、Darryl B McConnell

  DOI：10.1016/s0040-4020(00)00774-2

  日期：2000.10

  A range of 2'- and 7'-indolylglyoxylic amides 1 and 2, derived from 3-(4'-chlorophenyl)-4,6-dimethoxyindole, have been reduced to the corresponding alcohols 3 and 4 respectively. On treatment with acid, these alcohols underwent trimerisation to give the calix[3]indoles 8. The major conformer was generally the flattened partial cone, but in certain cases the cone conformers could be detected and even isolated. The related 2'-indolylglyoxylic amides 13, derived from 4,6-dimethoxy-3-methylindole, were also converted into calix[3]indoles 15. (C) 2000 Elsevier Science Ltd. All rights reserved.